Port · Puerto Rico

San Juan, Puerto Rico

San Juan was the walled Spanish capital of Puerto Rico, guarded by the fortress of San Felipe del Morro at the mouth of its bay. Around 1715 it was a garrison town paid for by silver from Mexico, on an island that lived mostly by cattle hides and smuggling. Its licensed privateers, the guardacostas, seized foreign ships, and enslaved people from nearby Danish, Dutch and English islands escaped there by sea in search of freedom.

What was San Juan like in 1715?

Juan Ponce de León founded the first Spanish town, Caparra, beside the bay in 1508. In 1521 the settlers moved to a rocky islet at the bay’s entrance, where Old San Juan stands today. Oddly, the names later swapped: the town was first called Puerto Rico (“rich port”) and the island San Juan, and over time people came to use them the other way round.

By the time Silver & Sails begins, San Juan was above all a military town. Spain valued it as a key guard post at the eastern edge of the Caribbean. Soldiers, officials, priests and craftsmen lived inside its walls, and a royal governor ruled the island from San Juan. His home was La Fortaleza, a fort built in 1537 that is still the governor’s residence today.

The whole island was thinly peopled, with roughly 20,000 inhabitants in 1700. The garrison was paid by the situado, a yearly subsidy sent from the silver treasury of Mexico. It often arrived late or not at all, which left soldiers and townspeople short of money.

How old is El Morro, and how was San Juan defended?

Castillo San Felipe del Morro, usually just called El Morro, was begun in 1539 on the headland that guards the narrow mouth of the bay. Builders kept enlarging and repairing it for about 250 years.

After a Dutch attack in 1625, Spain began a second great fort, San Cristóbal, and a ring of stone walls in 1634. According to the National Park Service, the whole city was enclosed by 1650. So in 1715 San Juan was already a walled city under El Morro.

Much of what visitors see today came later. After the officer Alexander O’Reilly inspected the defences in 1765, engineers spent about 25 years rebuilding them, and most of the bastions now standing date from 1765 to the 1780s. In 1983 the forts and La Fortaleza became a UNESCO World Heritage Site.

Was San Juan ever captured?

Yes, though not in the game’s years. In November 1595 the English raider Francis Drake attacked and was driven off. In 1598 George Clifford, Earl of Cumberland, landed an English force and took the city, but disease forced his men to leave after about two months.

In 1625 a Dutch fleet under Boudewijn Hendricksz seized the town and besieged El Morro for weeks. The fortress held, and the Dutch burned much of San Juan before sailing away. After that disaster, Spain walled the city. The National Park Service records no major attack on the forts between then and a failed British attack in 1797.

What did Puerto Rico trade around 1715?

Earlier, in the 1500s and 1600s, Puerto Rico grew sugar and ginger with the forced labour of enslaved Africans. By 1715 sugar had shrunk to a small business. Most of the land was given over to huge cattle ranches called hatos, and the island’s main export was cattle hides, used in Europe for leather. Ginger and tobacco were also grown.

Spain allowed its colonies to trade only with Spanish ships, and few came to Puerto Rico. So islanders bought cloth, tools, flour and other goods from English, French, Dutch and Danish traders instead, usually paying in hides, tobacco or cattle. In Spanish law this was smuggling. The historian Francisco Moscoso calls it the islanders’ main way of trading until well into the 1700s.

Read more about hides and deerskins and tobacco.

Who were Puerto Rico’s guardacostas?

Guardacostas (“coast guards”) were privately owned armed ships licensed by Spanish governors to stop foreign smugglers. The owners kept a share of what they seized, so the system rewarded captures, and foreign merchants complained that many seizures were simply robbery.

Puerto Rico’s most famous guardacosta owner was Miguel Enríquez, born in San Juan in the 1670s, the son of a freed woman of African descent. He trained as a shoemaker, then turned to privateering during the War of the Spanish Succession, when Spain had few warships of its own in the Caribbean. His fleet of fast sloops, schooners and brigantines took British, Dutch, Danish and French vessels. Captured cargoes sometimes included enslaved people, who were sold again rather than freed.

The king made Enríquez a Captain of Sea and War and awarded him a royal medal, and he became the richest man on the island. His captures were raised again and again in Britain’s House of Commons. In 1717 or 1718 his ships helped drive foreign settlers off the nearby island of Vieques. But when Spain wanted peace with Britain, he lost royal favour. From 1735 he lived in a San Juan convent to escape his enemies, and he died poor in 1743. The historian Ángel López Cantos, who studied his papers in Seville, calls him Puerto Rico’s first great national hero.

Why did enslaved people escape to Puerto Rico?

From the mid-1600s, enslaved people on the British, Dutch, French and Danish islands knew that Spanish colonies might take them in. Under a policy historians call religious sanctuary, a runaway who reached Spanish territory and asked to become a Catholic could be protected and, in many cases, freed. Spain issued orders for particular colonies in 1680, 1693 and 1704, and a decree of 1750 applied the rule across its whole empire.

The policy was not simple kindness. It drew workers to thinly settled Spanish lands and weakened rival plantation colonies. But historians stress that it was enslaved people themselves, by escaping, who drove Spain to make these laws.

Puerto Rico lay only a short sail from the Virgin Islands, where Denmark had settled St. Thomas in 1672. Many people escaped from there, from Dutch St. Eustatius and, later, from St. Croix in canoes and small boats. The historian Neville Hall called them “maritime maroons”: people who escaped slavery by sea. Some settled at San Mateo de Cangrejos, a free Black community just east of San Juan, today’s Santurce. Danish planters repeatedly asked for them back, often without success.

See also Charlotte Amalie on St. Thomas.

Legend or fact?

Legend says: El Morro looked in 1715 just as it does today.

Records show: El Morro was begun in 1539, but much of the fortress and walls now standing was rebuilt between 1765 and the 1780s.

Legend says: San Juan was never captured.

Records show: An English force under the Earl of Cumberland took the city in 1598, and the Dutch burned the town in 1625, although El Morro held out.

Legend says: Puerto Rico’s guardacostas were just pirates.

Records show: They sailed under licences from Spanish governors to stop smugglers. British merchants called them pirates, and some seizures were plainly unfair, but in Spanish law they were privateers.

Legend says: Puerto Rico was a great sugar island in 1715.

Records show: Sugar was small business then. Cattle hides were the main export, and sugar grew again only from the late 1700s.

Legend says: Spain freed every runaway who arrived, out of kindness.

Records show: Freedom depended on asking to become a Catholic, practice varied from place to place, and the rule covered the whole empire only from 1750. Spain also hoped to weaken its rivals.

Sources

  1. San Juan Timeline: Major Events for the Forts in San Juan, US National Park Service, San Juan National Historic Site. El Morro begun 1539; attacks of 1595, 1598 and 1625; walls begun 1634 and complete by 1650; O’Reilly in 1765, rebuilding 1765–1790 and the 1797 attack.
  2. San Juan Throughout Time, US National Park Service, San Juan National Historic Site. La Fortaleza (1537), El Morro, the walls and San Cristóbal; the 1625 Dutch attack.
  3. History & Culture, US National Park Service, San Juan National Historic Site. El Morro repaired and renovated for 250 years after 1539; San Cristóbal 1634–1790, mostly renovated 1765–1790.
  4. San Juan, Puerto Rico, Encyclopaedia Britannica. Caparra 1508, the move in 1521, the swap of names, the walls of 1634–1638 and bastions of 1765–1783.
  5. Puerto Rico: History, Encyclopaedia Britannica. Hides, ginger, sugar and tobacco; secret trade with non-Spanish merchants; a subsidy from the Mexican mines for San Juan’s forts from the later 1500s; Cumberland’s 1598 capture ended by disease.
  6. La Fortaleza and San Juan National Historic Site in Puerto Rico, UNESCO World Heritage Centre (1983). World Heritage listing of El Morro, San Cristóbal, the city walls and La Fortaleza.
  7. La industria ganadera en Puerto Rico durante los siglos XVI al XVIII, La Voz del Centro radio archive, with historian Francisco Moscoso (2021). Cattle ranches and hides as the main export; smuggling as the islanders’ main trade; population about 20,000 in 1700.
  8. Miguel Enríquez: el primer gran héroe nacional, La Voz del Centro radio archive, with historian Ángel López Cantos (author of Miguel Enríquez: corsario boricua del siglo XVIII, 1994) (2007). Enríquez’s origins, privateering, royal rank, debates in the House of Commons, fall from favour and death in poverty.
  9. Miguel Enríquez: corsario boricua del siglo XVIII, Ángel López Cantos (Ediciones Puerto) (1994). Archival biography of Enríquez: origins, privateering, royal honours, fall and death (cited via the radio interview and Wikipedia articles listed here).
  10. Loyal Catholics: Fugitive Slaves in the Caribbean and the Making of Spain’s Religious Sanctuary, Fernanda Bretones Lane, American Historical Association conference paper (2019). Flight from British, Dutch, French and Danish colonies to Spanish lands including Puerto Rico; conversion as the condition; the 1750 decree.
  11. Spain, the Caribbean, and the Making of Religious Sanctuary, Fernanda Bretones Lane, PhD dissertation, Vanderbilt University (2019). The sanctuary policy from the 1650s to the 1790s and the role of enslaved people’s own flight in creating it.
  12. Freedom at the fringes? Slave flight and empire-building in the early modern Spanish borderlands, Bram Hoonhout and Thomas Mareite, Slavery & Abolition (2018). Sanctuary orders of 1680, 1693 and 1704 and the decree of 1750; the Danish Virgin Islands and Puerto Rico as a sea border of escape, citing Neville Hall.
  13. Maritime Maroons: Grand Marronage from the Danish West Indies, N. A. T. Hall, in Slave Society in the Danish West Indies (University of the West Indies Press) (1992). Escape by sea from the Danish islands to Puerto Rico (cited via Hoonhout and Mareite).
  14. Puerto Rico Shares Some of St. Croix’s Rich Maroon History, Olasee Davis, St. Thomas Source (2022). Runaways from St. Croix escaping to Puerto Rico by canoe, refugees seen at San Mateo de Cangrejos, and failed Danish attempts to reclaim them.
  15. Charlotte Amalie, Encyclopaedia Britannica. Danish colony on St. Thomas from 1672.
  16. Miguel Enríquez (privateer), Wikipedia (citing López Cantos, 1994, and other histories of Puerto Rico). Additional source: birth in the 1670s to a freed mother, shoemaker’s training, the Vieques expedition, refuge in the convent from 1735 and death in 1743.
  17. Miguel Enríquez’s corsair fleet, Wikipedia (citing López Cantos, 1994; Moya Pons, 2007; Marley, 2008). Additional source: guardacostas as licensed coast guards, ship types, and British, Dutch, Danish and French prizes.
  18. Early Settlement of Puerto Rico (1493–1600), Casey Smith, open textbook, Cleveland State University Pressbooks. The situado from Mexico paid the San Juan garrison from 1582 and often arrived late.
  19. Captaincy General of Puerto Rico, Wikipedia (citing histories of colonial Puerto Rico). Additional source: the situado from New Spain often failed to arrive in the 1700s.
  20. San Mateo (Santurce), Wikipedia (citing San Mateo de Cangrejos, SUNY Press). Additional source: Cangrejos settled by self-freed people from St. Eustatius, St. Croix and St. Thomas.

Written for Silver & Sails. Facts last checked against these sources on 12 October 2026. Found a mistake? Tell us.